Cross-Coupling of Non-activated Chloroalkanes with Aryl Grignard Reagents in the Presence of Iron/N-Heterocyclic Carbene Catalysts
Sujit K. Ghorai, Masayoshi Jin, Takuji Hatakeyama and Masaharu Nakamura*
*International Research Center for Elements Science (IRCELS),
Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan, Email:
masaharu
scl.kyoto-u.ac.jp
S. K. Ghorai, M. Jin, T. Hatakeyama, M. Nakamura, Org. Lett., 2012, 14, 1066-1069.
DOI: 10.1021/ol2031729
see article for mor reactions
Abstract
A simple, efficient and high-yielding iron-catalyzed cross-coupling reaction of various primary, secondary, and tertiary alkyl chlorides with aryl Grignard reagents was achieved by using N-heterocyclic carbene ligands. A wide range of industrially abundant chloroalkanes can be converted, including polychloroalkanes, which are challenging substrates under conventional cross-coupling conditions.
see article for more examples
R. Agata, T. Iwamoto, N. Nakagawa, K. Isozaki, T. Hatakeyama, H. Takaya, M. Nakamura, Synthesis, 2015, 47, 1733-1740.
Iron-Catalyzed Cross-Coupling of Primary and Secondary Alkyl Halides with Aryl Grignard Reagents
M. Nakamura, K. Matsuo, S. Ito, E. Nakamura, J. Am. Chem. Soc., 2004, 126, 3686-3687.
Key Words
ID: J54-Y2012-0400
